(E)-N-(2-Bromo-5-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)vinyl)phenyl)-3-phenylpropanamide

ID: ALA4452808

PubChem CID: 142412490

Max Phase: Preclinical

Molecular Formula: C23H27BBrNO3

Molecular Weight: 456.19

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CC1(C)OB(/C=C/c2ccc(Br)c(NC(=O)CCc3ccccc3)c2)OC1(C)C

Standard InChI:  InChI=1S/C23H27BBrNO3/c1-22(2)23(3,4)29-24(28-22)15-14-18-10-12-19(25)20(16-18)26-21(27)13-11-17-8-6-5-7-9-17/h5-10,12,14-16H,11,13H2,1-4H3,(H,26,27)/b15-14+

Standard InChI Key:  JPZJMWMVVKRJFZ-CCEZHUSRSA-N

Molfile:  

 
     RDKit          2D

 29 31  0  0  0  0  0  0  0  0999 V2000
   19.2040  -19.3526    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.4186  -20.1450    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.9976  -19.5629    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6196  -20.6403    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8313  -20.8549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.4113  -21.4303    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0052  -21.5565    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0040  -22.3760    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7121  -22.7850    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4217  -22.3755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4189  -21.5529    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7103  -21.1476    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1251  -21.1416    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8343  -21.5475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5405  -21.1363    0.0000 B   0  0  0  0  0  0  0  0  0  0  0  0
   19.2876  -21.4646    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.6222  -20.3221    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.2960  -22.7840    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
   15.7119  -23.6022    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.0041  -24.0106    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0039  -24.8278    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2965  -23.6018    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.2961  -25.2362    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2959  -26.0534    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5882  -26.4595    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5877  -27.2760    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2958  -27.6856    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0060  -27.2727    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0030  -26.4577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  2  1  0
  5  4  1  0
  6  5  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12  7  1  0
 11 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 16  5  1  0
  5  2  1  0
  2 17  1  0
 17 15  1  0
  8 18  1  0
  9 19  1  0
 19 20  1  0
 20 21  1  0
 20 22  2  0
 21 23  1  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
 27 28  1  0
 28 29  2  0
 29 24  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4452808

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 456.19

Molecular Weight (Monoisotopic): 455.1267

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References

1. Verma K, Zang T, Penning TM, Trippier PC..  (2019)  Potent and Highly Selective Aldo-Keto Reductase 1C3 (AKR1C3) Inhibitors Act as Chemotherapeutic Potentiators in Acute Myeloid Leukemia and T-Cell Acute Lymphoblastic Leukemia.,  62  (7): [PMID:30836001] [10.1021/acs.jmedchem.9b00090]

2. Adeniji, Adegoke O AO and 5 more authors.  2011-03-01  Discovery of substituted 3-(phenylamino)benzoic acids as potent and selective inhibitors of type 5 17β-hydroxysteroid dehydrogenase (AKR1C3).  [PMID:21277203]

3. Adeniji, Adegoke O AO and 6 more authors.  2012-03-08  Development of potent and selective inhibitors of aldo-keto reductase 1C3 (type 5 17β-hydroxysteroid dehydrogenase) based on N-phenyl-aminobenzoates and their structure-activity relationships.  [PMID:22263837]

4. Brožič, Petra and 7 more authors.  2012-09-13  Selective inhibitors of aldo-keto reductases AKR1C1 and AKR1C3 discovered by virtual screening of a fragment library.  [PMID:22881866]

5. Hendriks, Christine M M and 7 more authors.  2015-10-15  Pentafluorosulfanyl-containing flufenamic acid analogs: Syntheses, properties and biological activities.  [PMID:26372652]

6. Pippione, Agnese C AC and 12 more authors.  2017-10-20  Hydroxytriazole derivatives as potent and selective aldo-keto reductase 1C3 (AKR1C3) inhibitors discovered by bioisosteric scaffold hopping approach.  [PMID:28881288]

7. Endo, Satoshi S and 16 more authors.  2017-10-26  Synthesis of Potent and Selective Inhibitors of Aldo-Keto Reductase 1B10 and Their Efficacy against Proliferation, Metastasis, and Cisplatin Resistance of Lung Cancer Cells.  [PMID:28976752]

8. Pippione, Agnese Chiara AC and 15 more authors.  2018-04-25  Potent and selective aldo-keto reductase 1C3 (AKR1C3) inhibitors based on the benzoisoxazole moiety: application of a bioisosteric scaffold hopping approach to flufenamic acid.  [PMID:29602039]

Source

Source(1):

• Scientific Literature